This research was initiated with the objective of investigating the potential impact of urban space design on play behavior and child development. Two neighborhoods (in Paris and Cairo) with similar spatial typologies (garden, pedestrian pathways, assembly zone, courtyard, building buffers, and pockets), but with different spatial attributes forming different configurations, were investigated. The study relies on causal comparative survey and intrinsic case study approaches. Data collection was conducted through children behavioral observations on children aged from 5 to 12 , perceptual drawing activities and informal interviews with child-led walks. The children are from middle socio-cultural segments of both societies that helped in understanding children’s play in a variety of outdoor settings. The assembled data was analyzed within the shadow of Trialectic Space and Affordances theories to the two neighborhoods, where children perception to their lived ambiance was identified. Trialectic theory helps in comprehending the difference between the conceived space by designers, the perceive space by children, and the resulted lived space. Affordance theory helps to link the environmental characteristics and the users’ behaviors according to their capabilities. Based on the analyzed data, the study identified a set of specific spatial physical aspects and functional qualities “potentialities” associated to children experiences and their space preferences. The study recommended that urban planners should extract themes essential for creating “child friendly” environment.